Happy 20th anniversary Conan O'Brien!

By Henry Hanks and Breeanna Hare, CNN

Updated 1:40 PM ET, Fri September 13, 2013

Conan O'Brien: Best late-night moments22 photos

In February 2015, Conan O'Brien took his show on the road to Havana, Cuba. It's just the latest triumph for the man who has been in late night TV for more than 20 years. Although he's had a bit of a rough ride -- what with 2010's late night wars over on NBC and all -- we've always made it a point to tune in to the guy behind Triumph the Comic Dog and the Masturbating Bear, no matter what channel he's on. Here are our some of our favorite moments from O'Brien's late night career.

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Conan O'Brien: Best late-night moments22 photos

Conan O'Brien introduced us to his wry mix of self-deprecating humor in September 1993, when he took over "Late Night" from David Letterman. After hearing repeatedly how much pressure was on him to be as funny as his predecessor, O'Brien good-naturedly accepted the ribbing before walking into his office to put a noose around his neck.

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Conan O'Brien: Best late-night moments22 photos

David Letterman made his first return appearance to NBC on "Late Night" in March 1994, and it's easily one of the first highlights of the show. Having both men in the same space was a classic that should be watched repeatedly.

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Conan O'Brien: Best late-night moments22 photos

Created by head writer Robert Smigel, Triumph the Insult Comic Dog took on a life of his own following his first appearance in 1997. He became one of Conan's most memorable recurring character.

In October 2000, Conan took Mr. T apple-picking, and the resulting segment was an instant classic. It was only nearly bested by the time Mr. T showed up during the "Late Night" 10th anniversary show and handed Conan a golden "7" for being funny 7 out of 10 years.

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Conan O'Brien: Best late-night moments22 photos

Jennifer Garner was infamously corrected by Conan O'Brien when she tried to tell him that "snuck" isn't a word. "Snuck isn't a word, Conan," Garner said in an aside during an anecdote. "You went to Harvard, you should know that." O'Brien responded by whipping out a dictionary, locating the entry for "snuck" and giving the "Alias" actress an education on its definition.

One of his most popular clips, Conan has name-checked his visit to an "old-fashioned baseball" league as one of his favorite segments. He even tried it out himself, probably one of the most memorable remote sketches.

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Conan O'Brien: Best late-night moments22 photos

When NBC and Universal became one, Conan got the genius idea to create the "Walker Texas Ranger" lever. He used it to show clips from Universal's "Walker" at any time in a nod to NBC Universal "corporate synergy."

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Conan O'Brien: Best late-night moments22 photos

Conan got a huge following in Finland when it turned out he resembled the country's female president, Tarja Halonen. After several weeks of joking about this, Conan went to Finland in 2006 and did an entire show from there, meeting the president.

When Conan shifted from "Late Night" to "The Tonight Show" in 2009, he again fashioned a classically funny transitional open: He "forgot" to move across the country to Los Angeles, so his first moments at 11:35 showed him running for his life across the country.

In December 2009, Sarah Palin made a surprise visit to "The Tonight Show" and returned a favor to William Shatner. Since Conan had the actor read dramatically from Palin's book "Going Rogue" during a sketch, Palin showed up to read from Shatner's autobiography "Up Till Now."

In January 2010, a beleaguered NBC wanted to move their failing prime-time show with Jay Leno back to 11:35, which would've knocked "The Tonight Show" to an unprecedented midnight hour. Conan wouldn't stand for it and opted to just bow out instead. The subsequent weeks leading up to his departure supplied extremely awkward yet must-see TV as Conan ripped NBC night after night.

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Conan O'Brien: Best late-night moments22 photos

When Conan departed NBC, he assured viewers that he didn't "regret a second" of his work on "Tonight." The final episode featured an emotional monologue from Conan, appearances from Steve Carell, Will Ferrell and Tom Hanks, and a rendition of "Free Bird."

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Conan O'Brien: Best late-night moments22 photos

After a wildly popular nationwide comedy tour in 2010, Conan debuted his new late night show on TBS to much fanfare. The cold open joked about Conan's NBC afterlife, which supposedly included doing a bunch of low-paying jobs and being a lazy bum around the house. (He even tried to get work at "Mad Men's" advertising world, where Jon Hamm as Don Draper reminded him that he has zero ad experience, and also, it's set in 1965 and Conan would be 2 years old.)

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Conan O'Brien: Best late-night moments22 photos

Conan O'Brien's "I've been fired!" beard briefly returned again in 2011, and ever loyal guest Will Ferrell made a huge fuss over shaving it. The Osama bin Laden raid had just happened, so Ferrell claimed the jubilant people in the streets were in reaction to the upcoming beard shaving.